Aryl(or heteroaryl) piperazinylalkylazole derivatives, their preparation and their application as medicaments
AssigneeLaboratorios Del Dr. Esteve, S.A.
InventorsRamon Merce-Vidal, Jordi Frigola-Constansa, Juan Pares-Corominas
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Abstract
The present invention relates to heterocyclic compounds, characterized in that they have the general formula I ##STR1## Wherein Ar, n and Z.sub.1 -Z.sub.6 are defined in the specification, are disclosed to have pharmaceutical activity on the central nervous system.
Claims8
A heterocyclic compound characterized in that it has the formula I ##STR25## in which n may have values 1 to 6,
- Ar represents an aromatic radical selected from the group consisting of phenyl, phenyl substituted with a methoxy or a halogen atom, a 3-(1, 2-benzisothiaxole radical) and a 2- N-methyl-imidazole radical,
- Z.sub.1 represents a nitrogen atom or a C-R.sub.1 group,
- Z.sub.2 represents a nitrogen atom or a C-R.sub.2 group,
- Z.sub.4 represents a nitrogen atom or a C-R.sub.4 group,
- Z.sub.5 represents a nitrogen atom, and
- Z.sub.6 represents a methylene group
- and R.sub.1, R.sub.2, R.sub.3 and R.sub.4, which may be identical or different, represent a hydrogen atom, a halogen atom, a lower alkyl radical, a carboxy radical, a carboxomide radical, an alkyl carboxylate radical or a phenyl radical.
A heterocyclic compound characterized in that it has the formula I ##STR26## in which AR represents the 2-pyrimidinyl radical, the five member ring structure together with R.sub.3 is imidazopyridine and Z.sub.6 represents a nitrogen atom or a carbon atom, each associated with a sufficient number of hydrogen atoms to satisfy its valence.
A heterocyclic compound characterized in that it has the formula II ##STR27## in which Z.sub.1 is nitrogen, Z.sub.2 is CH, R.sub.3 is chlorine, Z.sub.4 is CCl, R.sub.7 and R.sub.8 are hydrogen and R.sub.9 is a methoxy group.
A heterocyclic compound characterized in that it has the formula II ##STR28## in which Z.sub.1 is CMe, Z.sub.2 is nitrogen, R.sub.3 is chlorine, Z.sub.4 is CH, R.sub.7 is a methoxy group and R.sub.8 and R.sub.9 are hydrogen.
The compounds selected from the following group:
- -1-{4-[4-(2-pyrimidinyl)-1-piperazinyl]-butyl}-3H-imidazo[5,4-b]pyridine,
- -1-{4-[4-(2-pyrimidinyl)-1-piperazinyl]-butyl}-1H-imidazo{4,5-b]pyridine,
- -2-{4-[4-(2-pyrimidinyl)-1-piperazinyl]-butyl}-2H-benzothiazole,
- -4-chloro-1-{4-[4-(4-methoxyphenyl)-1-piperazinyl]-butyl}-1H-pyrazole,
- -4,5-dichloro-2-methyl-1-{4-[4-(4-methoxyphenyl) -1-piperazinyl]-butyl}-1H-imidazole,
- -4-chloro-1-{4-[4-(2-methoxyphenyl)-1-piperazinyl]-butyl}-1H-pyrazole,
- -4,5-dichloro-2-methyl-1-{4-[4-(2-methoxyphenyl) -1-piperazinyl]-butyl}-1H-imidazole,
- -4-chloro-1-{4-[4-(3-methoxyphenyl)-1-piperazinyl]-butyl}-1H-pyrazole,
- -1-{4-[4-(4-methoxyphenyl)-1-piperazinyl]-butyl}-pyrrole,
- -1-{4-[4-(2-methoxyphenyl)-1-piperazinyl]-butyl}-pyrrole,
- -1-{4[(4-phenyl)-1-piperazinyl]-butyl}-pyrrole,
- -4-chloro-1-{4-[4-phenyl-1-piperazinyl]-butyl}-1H-pyrazole,
- -4,5-dichloro-2-methyl-1-{4-[4-phenyl-1-piperazinyl]-butyl}-1-H-imidazole,
- -4-chloro-1-{4-[4-(2-chlorophenyl)-1-piperazinyl]-butyl}-1-H-pyrazole,
- -4,5-dichloro-2-methyl-1-{4-[4-(2-chlorophenyl)-1-piperazinyl]-butyl}-1H-im idazole,
- -4-chloro-1-}4-[4-(3-chlorophenyl)-1-piperazinyl]-butyl}-1H-pyrazole,
- -1-{4-[4-(2-N-methylimidazole)-1-piperazinyl]-butyl}-1H-pyrazole,
- -4-chloro-1-{2-[4-(2-methoxyphenyl)-1-piperazinyl]-ethyl}-1H-pyrazole,
- -4-chloro-1-{4-[4-(3-(1,2-benzisothiazolyl))-1-piperazinyl]-butyl}-1H-pyraz ole,
- -4,5-dichloro-2-methyl-1-{4-[4-(3-(1,2benzisothiazolyl))-1-piperazinyl]-but yl}-1H-imidazole.
Dependencies are inferred from the claim text.